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Publication numberUS4769481 A
Publication typeGrant
Application numberUS 07/017,029
Publication dateSep 6, 1988
Filing dateFeb 18, 1987
Priority dateSep 22, 1983
Fee statusLapsed
Also published asCA1234819A1, DE3334207A1, EP0135894A2, EP0135894A3, EP0135894B1
Publication number017029, 07017029, US 4769481 A, US 4769481A, US-A-4769481, US4769481 A, US4769481A
InventorsVolker Koch, Gerhard Burghardt
Original AssigneeHoechst Aktiengesellschaft
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
N-carbamoylaryl carboximidic acid esters, and their use as insecticides
US 4769481 A
Abstract
The compounds of the formula I ##STR1## in which R1 to R5 denote hydrogen; alkyl, alkoxy, alkylmercapto, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy each of which can be halogenated, halogen or nitro, R6 to R10 denote hydrogen; alkyl, alkoxy, alkenyloxy, alkylmercapto, alkenylmercapto, alkylsulfonyl or C3 -hydroxyalkyl each of which can be halogenated, (substituted) benzyloxy, alkoxycarbonyl or NRR', and R7 and R8 together can form a (substituted) alkylenedioxy radical,
X denotes OR11 in which R11 denotes optionally halogenated alkyl, cycloalkyl, alkenyl or alkynyl or optionally halogenated benzyl, or SR12 in which R12 denotes alkyl or benzyl each of which can be halogenated, and
Y denotes oxygen or sulfur, subject to the proviso that, if R1 and R5 both denote fluorine and R2, R3 and R4 denote hydrogen, the radicals R6 to R10 must not each represent halogenated (C1 -C6)-alkyl or halogen, possess an intense action against a broad spectrum of harmful insects.
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Claims(9)
We claim:
1. A compound of the formula I ##STR20## wherein R1 is hydrogen, fluorine or chlorine, R2, R3 and R4 are hydrogen, R5 is fluorine or chlorine, R6 and R10 are hydrogen, R8 is halogenated (C1 -C6)-alkoxy or halogenated (C1 -C6)-alkylmercapto, R7 and R9 are chlorine, X is (C1 -C6)-alkoxy and Y is oxygen.
2. The compound as claimed in claim 1 wherein R8 is selected from the group consisting of OCF2 CHF2, OCF2 CHCl2, OCF2 CHClF, OCF2 CHBrF or OCF2 CHFCF3 and X is (C1 -C4)-alkoxy.
3. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate.
4. The compound as claimed in claim 1, wherein R8 is halogenated (C1 -C6)-alkylmercapto.
5. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate.
6. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate.
7. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate.
8. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate.
9. The compound as claimed in claim 1, which is O-ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate.
Description

This application is a continuation of application Ser. No. 653,692, filed Sept. 21, 1984, abandoned.

It is already known that certain N-carbamoyl-2,6-difluorobenz(thio)carboximidic acid esters have insecticidal properties (European Pat. No. 5,944). There are, however, disadvantages in the use of these, such as insufficient activity.

New substituted N-(thio)carbamoylaryl(thio)carboximidic acid esters having advantageous insecticidal properties have now been found.

The present invention relates, therefore, to the compounds of the formula I ##STR2## in which R1 to R5 independently of one another denote hydrogen; (C1 -C6)-alkyl, (C1 -C6)-alkoxy, (C1 -C6)-alkylmercapto, (C1 -C6)-alkylsulfinyl, (C1 -C6)-alkylsulfonyl or (C1 -C6)-alkylsulfonyloxy, it being possible for the abovementioned radicals to be monosubstituted or polysubstituted by halogen; or halogen or nitro,

R6 to R10 independently of one another denote hydrogen; (C1 -C6)-alkyl, (C1 -C6)-alkoxy, (C1 -C6)-alkenyloxy, (C1 -C6)-alkylmercapto, (C1 -C6)-alkenylmercapto, (C1 -C6)-alkylsulfonyl or C3 -hydroxyalkyl, it being possible for the abovementioned radicals to be monosubstituted or polysubstituted by halogen; benzyloxy which can be substituted by halogen, (C1 -C6)-halogenoalkyl, (C1 -C6)-halogenoalkoxy, cyano or nitro; (C1 -C9)-alkoxycarbonyl;

NRR' in which R and R' independently of one another denote (C1 -C6)-alkyl, (C3 -C6)-alkenyl or (C3 -C6)-alkynyl, it being possible for these substituents to be monosubstituted or polysubstituted by halogen, or denote halogen, nitro or cyano, or R and R', together with the common nitrogen atom, form a saturated 5-membered ring or 6-membered ring which can contain oxygen, sulfur or NR" as a ring member and which can be substituted by (C1 -C3)-alkyl, R" denoting (C1 -C3)-alkyl, and

R7 and R8 together can form a (C1 -C2)-alkylenedioxy radical which can be substituted by halogen and CF3,

X denotes OR11 in which R11 denotes optionally halogenated (C1 -C6)-alkyl, (C5 -C6)-cycloalkyl, (C3 -C6)-alkenyl, (C3 -C6)-alkynyl or optionally halogenated benzyl, or

X denotes SR12 in which R12 denotes (C1 -C6)-alkyl or benzyl which can be monosubstituted or polysubstituted by halogen, and

Y denotes oxygen or sulfur, subject to the proviso that, if R1 and R5 both denote fluorine and R2, R3 and R4 denote hydrogen, the radicals R6 to R10 must not each represent halogenated ((C1 -C6)-alkyl or halogen.

The following are examples of compounds, according to the invention, of the formula I:

Ethyl N-[N-(2-fluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2-fluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2-ethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-benzcarboximidate

Ethyl N-[N-(3-nitrophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-(nitrophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(3-(1,1,1,3,3,3-hexafluoro-2-propylamino)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(b 3-methoxycarbonylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-difluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-fluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

2-Propyl N-[N-(4-fluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorophenyl)-carbamoyl]-benzcarboximidate

Propargyl N-[N-(4-chlorophenyl)-carbamoyl]-benzcarboximidate

Ethyl N-[N-(4-chlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Methyl N-[N-(4-chlorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxyphenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxyphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-benzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

1-Propyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

1-Butyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

1-Hexyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Cyclohexyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-3-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-4-chlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-iodobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

1-Hexyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,5-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-pentafluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chloro-6-methoxybenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyhenyl)-carbamoyl]-2-fluoro-5-nitrobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chloro-5-nitrobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-methanesulfonyloxybenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-4-trifluoromethoxybenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-3-trifluoromethoxybenzcarboximidate

Ethyl N-[N-4-trifluoromethoxyphenyl)-carbamoyl]-2-methoxybenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-4-(1,1-difluoro-2,2,2-trichloroethoxy)-benzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-difluoromethylmercaptobenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-3-nitro-5-trifluoromethylbenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-trifluoromethylbenzcarboximidate

Methyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-3-trifluoromethylcarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-methylbenzcarboximidate

Propargyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-benzcarboximidate

2,2,2-Trifluoroethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-benzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethylmercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-difluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercaptophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylmercaptophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethyl)-mercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethyl)-mercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethyl)-mercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethyl)-mercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethyl)-mercaptophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2-chloro-b 5-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethyl)-mercaptophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propyl)-mercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexfluoro-1-propyl)-mercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propyl)-mercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propyl)-mercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propyl)-mercaptophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylsulfonylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylsulfonylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-trifluoromethylsulfonylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-nitrophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-nitrophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-nitrophenyl)-carbamoyl]-2,6-difluorocarboximidate

Ethyl N-[N-(4-nitrophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-nitrophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-trifluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-trifluorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)-phenyl-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(methoxycarbonylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(ethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1-dimethylethyl)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(4-(chlorophenyl)-thiocarbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(4-trifluoromethoxyphenyl)-carbamoyl]-2-fluorobenzthiocarboximidate

Ethyl N-[N-(4-trifluoromethoxyphenyl)-carbamoyl]-2-chlorobenzthiocarboximidate

Ethyl N-[N-(4-trifluoromethylphenyl)-carbamoyl]-2-chlorobenzthiocarboximidate

Ethyl N-[N-(2,3-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2-chloro-3-methylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(2,4-difluorophenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(2,4-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlor-2-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2-chlor-4-(2-propyl-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-bis-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2-chloro-5-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,5-difluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,5-difluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,6-difluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,6-dichlorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,6-dibromophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,6-dimethoxyphenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,6-dimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,6-dimethylphenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2-ethyl-6-methylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2-ethyl-6-methylphenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(3-chloro-4-fluorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-fluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-fluoro-3-nitrophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(3,5-dimethyl-1-piperidinyl)-3-fluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(3,5-dimethyl-1-piperidinyl)-3-fluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(3,5-dimethyl-1-piperidinyl)-3-fluorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-trifluoromethoxy-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-trifluoromethoxy-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-trifluoromethoxy-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzbenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-trifluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethylmercapto)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chloro-3-trifluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(3,5-dimethyl-1-piperidinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4(-bis-(2-butyl)-amino)-3-chlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-cyanophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1-dimethylethoxycarbonyl)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2,4-dimethyl-3-pentyloxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(3,5,5-trimethyl-1-hexyloxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-methylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-3-fluorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-iodobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-chloro-5-nitrobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2,5-dichlorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-pentafluorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-3-trifluoromethoxybenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-4-trifluoromethoxybenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-methoxybenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-3-nitro-5-trifluorobenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-trifluoromethylbenzcarboximidate

Ethyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-3-trifluoromethylbenzcarboximidate

Ethyl N-[N-(4-trifluoromethoxy-3-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-3-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-3-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximide

Ethyl N-[N-(3,4-bisdifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,4-bistrifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,2-difluorobenzo[1,3]dioxol-5-yl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2H,3H-2,2,3-trifluorobenzo[1,4]dioxin-6-yl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2H,3H-3-chloro-2,2,3-trifluorobenzo[1,4]-dioxin-6-yl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2H,3H-2,2,3,3-tetrafluorobenzo[1,4]dioxin-6-yl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2H,3H-2,2,3,3-tetrafluorobenzo[1,4]dioxin-6-yl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2H,3H-2,2,3,3-tetrafluorobenzo[1,4]dioxin-6-yl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2H,3H-2,2-difluoro-3-trifluoromethylbenzo[1,4]-dioxin-6-yl)-carbamoyl]-2,6-fluorobenzcarboximidate

Ethyl N-[N-(3-methyl-4-(1-piperidinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,4-dimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Methyl N-[N-(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-2-chlorobenzthiocarboximidate

Methyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-fluorobenzthiocarboximidate

Methyl N-[N-(3,4-dichlorophenyl)-carbamoyl]-2-chlorobenzthiocarboximidate

Ethyl N-[N-(3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-bistrifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethylphenyl)-carbamoyl]-2-fluorobenzcarboximide

Ethyl N-[N-(3-ethylsulfonyl-5-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,3-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(4-chloro-2-fluoro-5-(2-propoxy)-phenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(5-chloro-2,4-difluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(5-chloro-2,4-difluorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(5-chloro-2,4-difluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(5-chloro-2,4-difluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(5-chloro-2,4-difluorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(5-bromo-2-chloro-4-methylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4,5-trichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4,6-trifluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,4,6-trifluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(2,4,6-trichlorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(3-chloro-4-(3-chloro-2-propen-1-yloxy)-5-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(3-bromo-2-propen-1-yloxy)-5-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-5-methylphenyl)-carbamoyl]-2-trifluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-5-methylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3-chloro-1,1,2-trifluoroethoxy)-5-methylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-5-methylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-5-methyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-5-methyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate Ethyl N-[N-(3-chloro-5-methyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-5-methyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl)-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-5-methylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-5-methylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-5-methylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-5-methylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-bistrifluoromethyl-4-chlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3-bromo-4-(3-chloro-2-propen-1-yloxy)-5-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-bromo-4-(2-propen-1-yloxy)-5-trifluoromethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-bromo-5-chloro-4-(3-chloro-2-propen-1-yloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-bromo-5-chloro-4-(2-propen-1-yloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxy-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chloro-6-methoxybenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-3,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-3,5-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-bis-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-methoxybenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-difluoromethylmercaptobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-difluoromethylsulfinylbenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-difluoromethylsulfonylbenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-trifluoromethylbenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-methylbenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Benzyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

4-Chlorobenzyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Methyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

2,2,2-Trifluoroethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-carbamoyl]-2-fluorobenzcarboximidate

2,2,2-Trichloroethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluoro-5-nitrobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-4-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl-N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl-N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chloro-6-methoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl-N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-3,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-3,5-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-bis-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-methoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-methylsulfonyloxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-difluoromethylmercaptobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-difluoromethylsulfinylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-difluoromethylsulfonylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-methylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-trifluoromethylbenzcarboximidate

1-Propyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Allyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Propargyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

1-Butyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

1-Hexyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Cyclohexyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2,2-dibromo-1,1-difluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorocarboximidate

Ethyl N-[N-(4-(2,2-dichloro-1,1-difluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1-difluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Cyclohexyl N-[N-(3,5-dichloro-4-pentafluoroethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloro-1,2-difluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chloro-6-methoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-3,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-3,5-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-bis-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-methoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-difluoromethylmercaptobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-difluoromethylsulfinylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-difluoromethylsulfonylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-trifluoromethylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-methylbenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,4,4,4-octafluoro-1-butoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,2-trifluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,3-tetrafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,3-tetrafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,3-tetrafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,3-tetrafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,4,4,4-hexafluoro-1-butoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,3,4,4,4-heptafluoro-1-butoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,2,3,4,4,5,5,5-octafluoro-1-pentoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(4-chlorobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(4-chlorobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-trifluoromethylbenzyloxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-trifluoromethylbenzyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(3-chloro-4-trifluoromethylbenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(3-chloro-4-trifluoromethylbenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-4-trifluoromethylbenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-4-trifluoromethylbenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-nitrobenzyloxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-nitrobenzyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2,4-dichlorobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2,4-dichlorobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(4-cyanobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(4-cyanobenzyloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-trifluoromethoxybenzyloxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-trifluoromethoxybenzyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-benzyloxy-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-fluorobenzyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-pentafluorobenzyloxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,2-dichloroethenyloxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(3-chloro-2-propen-1-yloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(3-bromo-2-propen-1-yloxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-allyloxy-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-difluoromethylmercaptophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercapto-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercapto-3,5-dichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethylmercapto-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-trifluoromethylmercaptophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-trifluoromethylmercaptophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-trifluoromethylmercaptophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoromethylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoromethylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoromethylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoromethylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethylmercapto)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethylmercapto)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethylmercapto)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethylmercapto)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3,-hexafluoro-1-propylmercapto)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propylmercapto)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propylmercapto)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propylmercapto)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(3-bromo-2-propen-1-ylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(3-chloro-2-propen-1-ylmercapto)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1-pyrrolidinyl)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1-pyrrolidinyl)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1-pyrrolidinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1-pyrrolidinyl)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-morpholinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(4-methyl-1-piperazinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dibromo-4-(1-pyrrolidinyl)-pyrrolidinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dibromo-4-(1-piperidinyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-allyl,N-methylamino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(4-allyl,N-(1-butyl)-amino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N,N-dimethylamino)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-(3-chloroallyl,N-methylamino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-(3-bromoallyl,N-methylamino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-(3-bromoallyl,N-methylamino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-(3-bromoallyl,N-(1-butyl)-amino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(N-(3-chloroallyl),N-(butyl)-amino)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N-methyl,N-propargylamino)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N-ethyl,N-propargylamino)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N,N-dipropargyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N-methyl,N-(1-propyl)-amino)-phenyl)-carbamoyl]-2,6-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(N-methyl,N-(1-propyl)-amino)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-cyano-3,5-dichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-cyano-3,5-dichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-cyano-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-cyano-3,5-dichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1-dimethylethoxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(2,4-dimethyl-3-pentyloxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1-heptyloxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(3,5,5-trimethyl-1-hexyloxycarbonyl)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy-3,5-dibromophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dibromo-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dibromo-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-bistrifluoromethyl-4-difluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-bistrifluoromethyl-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl)-carbamoyl]-2,6-fluorobenzcarboximidate

Ethyl N-[N-3,5-bistrifluoromethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-bistrifluoromethyl-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxy-3,5-dimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxy-3,5-dimethylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dimethylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dimethylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chloro-B 4-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dimethyl-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-1,2-dichloroethenyloxy)-3,5-dimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3-chloro-4-(1,2-dichloroethenyloxy)-5-methylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-thiocarbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-thiocarbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-thiocarbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-carbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-thiocarbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichlorophenyl)-thiocarbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-thiocarbamoyl]-2,6-difluorobenzthiocarboximidate

Ethyl N-[N-(3,5-dichloro-4-(difluoromethoxy)-2-fluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxy-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoromethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-3,5-dichloro-2-fluorophenyl)-carbamoyl]-2-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-phenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-5-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-difluoromethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-(2,2,2-trifluoroethoxy)-benzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(3,5-dichloro-2,4-difluorophenyl)-carbamoyl]-2-difluoromethylmercaptobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)-carbamoyl]-2,4-difluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)-carbamoyl]-2-chloro-5-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrafluorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-dichloro-3-difluoromethyl-5-trifluoromethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,4-dichloro-3-difluoromethyl-5-trifluoromethylphenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2,4-dichloro-3-difluoromethyl-5-trifluoromethylphenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(2,4-dichloro-3-difluoromethyl-5-trifluoromethylphenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-difluoromethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-chlorodifluoromethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2,6-difluorobenzacarboximidate

Ethyl N-[N-(2,3,5-trichloro-4-trifluoromethoxyphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-bromo-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N -(4-(1,1,2,2-tetrafluoroethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy-2,3,5-trichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(b 4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trichlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-chlorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-chlorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-chlorophenyl)-carbamoyl]-4-chloro-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-chlorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-chlorophenyl)-carbamoyl]-2-chloro-4-fluorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(2,3,4,5-tetrachlorophenyl)-carbamoyl]-b 2,6-dichlorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(2-chloro-1,1,2-trifluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,2-tetrafluoroethoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(4-(1,1,2,3,3,3-hexafluoro-1-propoxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,4-dichlorobenzcarboximidate

Ethyl N-[N-(4-(1,2-dichloroethenyloxy)-2,3,5-trimethylphenyl)-carbamoyl]-2,6-difluorobenzcarboximidate

Ethyl N-[N-(2,3,5,6-tetrafluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(2,3,5,6-tetrafluorophenyl)-carbamoyl]-2-chlorobenzcarboximidate

Ethyl N-[N-(2,3,5,6-tetrafluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(2,3,5,6-tetrafluorophenyl)-carbamoyl]-2,6-dimethoxybenzcarboximidate

Ethyl N-[N-(pentafluorophenyl)-carbamoyl]-2-fluorobenzcarboximidate

Ethyl N-[N-(pentafluorophenyl)-carbamoyl]-2-chloro-6-fluorobenzcarboximidate

Ethyl N-[N-(pentafluorophenyl)-carbamoyl]-2,6-dichlorobenzcarboximidate

The present invention also relates to a process for the preparation of the compounds of the formula (I) which comprises

(a) reacting substituted aryl(thio)carboximidic acid esters of the formula (II) ##STR3## in which R1 to R5 and X have the same meanings as in formula (I), with compounds of the formula (III) ##STR4## or with compounds of the formula (IV) ##STR5## in which R6 to R10 and Y have the same meanings as in formula (I) and Z1 denotes a basic leaving group other than halogen, such as, for example, (C1 -C3)-alkoxy or phenoxy which can be halogenated, imidazole or triazole,

or

(b) reacting substituted aryl(thio)carboximidic acid ester derivatives of the formula (V) ##STR6## in which R1 to R5, X and Y have the same meanings as in formula (I) and Z2 has the same meaning as Z1 and additionally represents halogen, with substituted anilines of the formula (VI) ##STR7## in which R6 to R10 have the same meanings as in formula (I), or (c) reacting substituted 1,3,5-oxadiazine derivatives of the formula (VII) ##STR8## in which R1 to R10 and Y have the same meanings as in formula (I), with substituted hydroxy or mercapto compounds of the formulae (VIII) or (IX), respectively,

R11 OH                                                (VIII)

R12 SH                                                (IX)

in which R11 and R12 have the same meanings as in formula (I).

The aryl(thio)carboximidic acid esters of the formula (II) to be used as the starting compounds in process of preparation (a) are in part novel and can be prepared by processes which are known per se from the literature:

1. By acid catalyzed or base-catalyzed addition of compounds of the formula (VIII) or (IX) to the substituted nitriles of the formula (X) in which R1 to R5 have the meaning indicated above. ##STR9## (see R. Rogers, Chem. Rev. 61, 179 (1961))

2. By transesterifying readily accessible benz(thio)carboximidic acid esters of the formula (II) with compounds of the formula (VIII) or (IX) in which R1 to R5 and R11 and R12 have the meaning indicated above (R. J. Kauffmann, J. Am. Chem. Soc. 45, 1744 (1923)).

3. By O-alkylating or S-alkylating substituted (thio)-amides of the formula (XI) in which R1 to R5 and Y have the meaning indicated above ##STR10## (M. Matsui, Brit. Chem. Abstract 98, 695 (1910) and H. Meerwein, J. prakt. Chem. 154, 154 (1940)).

The compounds of the formula (III) and (IV) to be used as the starting compounds in the process of preparation (a) are either known or can be prepared analogously to processes known from the literature (Houben-Weyl, Volume VIII, 1952; Houben-Weyl, Volume E 4, 1983).

The substituted arylcarboximido(thio)ester derivatives of the formula (V) to be used as the starting compounds in process of preparation (b) are accessible in a manner known per se from compounds of the formula (II) (Houben-Weyl, Volume E 4, 1983). The aniline of the formula (VI) required for route (b) are either known or can be prepared by processes known per se from the literature (Houben-Weyl, Volume XI/1 (1957)).

The 1,3,5-oxadiazine derivatives of the formula (VII) to be used as the starting compounds in process of preparation (c) are obtainable by processes known per se from the literature (U.S. Pat. No. 4,150,158).

The process variant (a), mentioned for the preparation of N-amino(thio)carbonylarylbenz(thio)carboximidic acid esters of the formula (I), is carried out with, or preferably without, a diluent. Suitable diluents are virtually all aprotic solvents. These include, in particular, aliphatic and aromatic and, if appropriate, halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers, such as diethyl and dibutyl ethers, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, such as methyl and ethyl acetate, nitriles, such as, for example, acetonitrile and propionitrile, amides, such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

The reaction temperature is, in general, between -10° C. and +150° C., preferably between +10° C. and 105° C.

The starting materials are usually employed in equimolar amounts. An excess of either reactant is, however, possible.

In process variant (b), the reaction is preferably carried out in a diluent. Suitable diluents are all neutral, non-nucleophilic organic solvents, but preferably those mentioned for process (a).

The reaction temperature is, in general, between -10° C. and +140° C., preferably between +10° C. and +80° C.

As in process (a), the starting materials are usually employed in equimolar amounts. An excess of either reactant is, however, possible.

In the preparation of the compounds of the formula (I) by process variant (c), the reaction of the compounds of the formula (VII) with the components (VIII) is advantageously carried out in an excess of the component (VIII).

In the reaction of substances of the formula (VII) with compounds of the formula (IX), equimolar amounts are usually employed and the reaction is advantageously carried out in a diluent which has already been mentioned under process variant (a).

The reaction temperature is, in general, between +20° C. and +150° C., preferably between +50° C. and +100° C.

The isolation and, if required, purification of the compounds of the formula (I) is effected by methods which are generally customary, for example by evaporating off the solvent (if appropriate under reduced pressure) and subsequently recrystallizing the residue, or by chromatography.

The compounds of the formula (I) are obtained in these reactions as E-isomers or Z-isomers or E/Z-mixtures. The E/Z-mixtures can be separated by physical processes known per se, such as fractional crystallization. Both isomers are biologically active and both are therefore embraced by the present invention.

The compounds of the formula (I) are readily soluble in most organic solvents.

The active compounds are well tolerated by plants and have an advantageous toxicity to warm-blooded animals and are suitable for controlling animal pests, in particular insects, arachnids and nematodes, and very particularly preferentially for controlling insects which occur in agriculture, in forestry, in the protection of stocks and materials and in the field of hygiene. They are effective against normally sensitive and resistant species and against all or individual stages of development. The pests mentioned above include the following:

From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of Diplopoda, for example Blaniulus guttulatus.

From the order of Chilopoda, for example Geophilus carpophagus and Scutigera species.

From the order of Symphyla, for example Scutigerella immaculata.

From the order of Thysanura, for example Lepisma saccharina.

From the order of Collembola, for example Onychiurus armatus.

From the order of Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa species, Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of Dermaptera, for example Forficula auricularia.

From the order of Isoptera, for example Reticulitermes species.

From the order of Anoplura, for example Phylloera vastatrix, Phemphigus species, Pediculus humanus corporis, Haematopinus species and Linognathus species.

From the order of Mallophaga, for example Trichodectes species and Damalinea species.

From the order of Thysanoptera, for example Hercinothrips femoralis and Thrips tabaci.

From the order of Heteroptera, for example Eurygaster species, Dysdercus intermedius, Piesma quadrata, Cimex Lectularius, Rhodnius prolixus and Triatoma species.

From the order of Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Bravicornyne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphium avenae, Myzus species, Phorodon humuli, Rhopalosiphum padi, Empoasca species, Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella auroantii, Aspidiotus hederae, Pseudococcus species and Psylla species.

From the order of Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria species, Buceulatrix thurberiella, Phyllocnistis citrella, Agrotis species, Euxoa species, Feltia species, Earias insulana, Heliothis species, Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera species, Trichoplusia ni, Carpocapsa pomonella, Pieris species, Chilo species, Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

From the order of Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochlearieae, Diabrotica species, Psylliodes chrysocephala, Epilachna varivestis, Atomaria species, Oryzaephilus surinamensis, Anthonomus species, Sitophilus species, Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes species, Trogoderma species, Anthrenus species, Attagenus species, Lyctus species, Meligethes aeneus, Ptinus species, Niptus hololeucus, Gibbium psylloides, Tribolium species, Tenebrio molitor, Agriotes species, Conoderus species, Melolontha melolontha, Amiphimallon solstitialis and Costelytra zealandica.

From the order of Hymenoptera, for example Diprion species, Hoplocampa species, Lasius species, Monomorium pharaonis and Vespa species.

From the order of Diptera, for example Aedes species, Anopheles species, Culex species, Drosophila melanogaster, Musca species, Fannia species, Calliphora erythrocephala, Lucilia species, Chrysomyia species, Cuterebra species, Gastrophilus species, Hyppobosca species, Stomoxys species, Oestrus species, Hypoderma species, Tabanus species, Tannia species, Bibio hortulanus, Oscinella frit, Phorbia species, pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of Siphonaptera, for example Xenopsylla cheopis and Ceratophyllus species.

From the order of Arachnida, for example Scorpio maurus and Latrodectus mactans.

The invention also relates to agents containing the compounds of the formula I as well as suitable formulation auxiliaries.

The agents according to the invention generally contain 1-95% by weight of the active compounds of the formula I. They can be applied in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting agents or granules.

Wettable powders are preparations which can be dispersed uniformly in water and which, in addition to the active compound and also a diluent or inert substance, also contain wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleylmethyltaurate.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatic compounds or hydrocarbons, with the addition of one or more emulsifier. The following are examples of emulsifiers which can be used: calcium salts of alkylarylsulfonic acids, such as Ca dodecylbenzenesulfonate, or nonionic emulsifier, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, fatty acid esters of sorbitan, fatty acid esters of polyoxyethylenesorbitan or esters of polyoxyethylenesorbitol.

Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite or pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto an adsorptive, granulated inert material or by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers, such as sand, kaolinite or granulated inert material. It is also possible to prepare suitable active compounds in the manner customary for the production of fertilizer granules--if desired as a mixture with fertilizers.

In their commercially available formulations and in the application forms prepared from these formulations, the active compounds according to the invention can be in the form of a mixture with other active compounds, such as insecticides, attractants, sterilizers, acaricides, nematocides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example: phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, and others.

The content of active compound in the application forms prepared from the commercially available formulations can vary within wide ranges. The concentration of active compound in the application forms can be from 0.0000001 to 100% by weight of active compound, preferably between 0.00001 and 1% by weight.

Application is effected in a customary manner suited to the application forms.

The active compounds according to the invention are also suitable for controlling ectoparasites and endoparasites, preferably ectoparasitic insects in the field of veterinary medicine or in the field of animal husbandry.

The application of the active compounds according to the invention is effected in this case in a known manner, such as by oral administration in the form of, for example, tablets, capsules, drink or granules, dermal application in the form of, for example, dipping, spraying, pouring on and spotting on and powdering on, and parenteral administration in the form of, for example, injection.

The new compounds, according to the invention, of the formula I can accordingly also be employed with particular advantage in animal husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the new compounds, if appropriate in suitable formulations (cf. above) and, if appropriate, together with the drinking water or feed, are administered to the animals orally. Since excretion in the feces takes place in an effective manner, the development of insects in the feces of the animals can be prevented very simply in this manner. The dosages and formulations suitable in a particular case depend particularly on the nature and stage of development of the livestock and on the intensity of infestation by insects, and can be determined and established easily by the customary methods. In the case of cattle, for example, the new compounds can be employed in dosage amounts of 0.01 to 1 mg/kg of body weight.

The following Examples serve to illustrate the invention.

A. FORMULATION EXAMPLES

(a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance, and comminuting the mixture in a beater mill.

(b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting and dispersing agent, and grinding the mixture in a pinned disc mill.

(c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 20 parts by weight of active compound with 6 parts by weight of an alkylphenol polyglycol ether (Triton×207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of a paraffinic mineral oil (boiling range, for example, approx. 255° to over 377° C.), and grinding the mixture in an abrasion ball mill to a fineness of less than 5 microns.

(d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as an emulsifier.

(e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granular carrier, such as attapulgite, pumice granules and/or quartz sand.

  B. Chemical Examples              M.P. (°C.) Example of E/Z- No. R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 X Y mixture   1 F H H H F F H H H H OC2 H5 O 93-95 2 OCH3 H H H OCH3 F H H H H OC2 H5 O 143-145 3 F H H H H OC2 H5 H H H H OC2 H5 O 77 4 H H H H H H OCF2 CHF2 H H H OC2 H5 O 62 5 F H H H F H NO2 H H H OC2 H5 O 128 6 F H H H Cl H NO2 H H H OC.sub. 2 H5 O 110  7 F H H H H H  ##STR11##  H H H OC2 H5 O 94  8 F H H H H H COOCH3 H H H OC2 H5 O 100 9 F H H H H H CHF2 H H H OC2 H5 O 102 10 F H H H H H CF3 H H H OC2 H5 O 120 11 F H H H H H H F H H OC2 H5 O 78-80 12 H H H H H H H Cl H H OC2 H5 O 128 13 H H H H H H H Cl H H OCH2CH O 114 14 F H H H H H H Cl H H OC2 H5 O 130-132 15 F H H H H H H OCHF2 H H OC2 H5 O 109 16 Cl H H H H H H OCHF2 H H OC2 H5 O 80 17 F H H H F H H OCHF2 H H OC2 H5 O 89 18 F H H H Cl H H OCHF2 H H OC2 H5 O 88 19 Cl H H H Cl H H OCHF2 H H OC2 H5 O 95 20 F H H H H H H OCClF2 H H OC2 H5 O 93-95 21 H H H H H H H OCF3 H H OC2 H5 O 85 22 F H H H H H H OCF3 H H OCH3 O 125-127 23 F H H H H H H OCF3 H H OC2  H5 O 97-99 24 F H H H H H H OCF3 H H O(CH2)2 CH3 O 84 25 F H H H H H H OCF3 H H O(CH2)3 CH3 O 105 26 F H H H H H H OCF3 H H O(CH2)5 CH3 O 69-71 27 F H H H H H H OCF3 H H  ##STR12##  O 130-132   28 H F H H H H H OCF3 H H OC2 H5 O 56 29 Cl H H H H H H OCF3 H H OC2 H5 O 86-87 30 H H Cl H H H H OCF3 H H OC2 H5 O 110 31 I H H H H H H OCF3 H H OC2 H5 O 115 32 F H F H H H H OCF3 H H OC2 H5 O 91 33 F H H H F H H OCF3 H H OC2 H5 O 90-99 34 F H H H F H H OCF3 H H O(CH2)5 CH3 O 71 35 F H Cl H H H H OCF3 H H OC2 H5 O 99 36 F H H Cl H H H OCF3 H H OC2 H5 O 113 37 F H H H Cl H H OCF3 H H OC2 H5 O 88 38 Cl H F H H H H OCF3 H H OC2 H5 O 79 39 Cl H H F H H H OCF3 H H OC2 H5 O 92 40 Cl H Cl H H H H OCF3 H H OC2 H5 O 91 41 Cl H H Cl H H H OCF3 H H OC2 H5 O 110 42 Cl H H H Cl H H OCF3 H H OC2 H5 O 99-102 43 F F F F F H H OCF3 H H OC2 H5 O 123-125 44 Cl H H H OCH3 H H OCF3 H H OC2 H5 O 130 45 F H H NO2 H H H OCF3 H H OC2 H5 O 102-105 46 Cl H H NO2 H H H OCF3 H H OC2 H5 O 150 47 CH3 SO2 O H H H H H H OCF3 H H OC2 H5 O 94-96 48 CHF.sub. 2 O H H H H H H OCF3 H H OC2 H5 O 87 49 H H CF3 O H H H H OCF3 H H OC2 H5 O 97 50 H CF3 O H H H H H OCF3 H H OC2 H5 O 82 51 CH3 O H H H H H H OCF3 H H OC2 H5 O 104 52 H H CCl3 CF2 O H H H H OCF3 H H OC2 H5 O 118 53 CHF2 S H H H H H H OCF3 H H OC2 H5 O 92 54 H NO2 H CF3 H H H OCF3 H H OC2 H5 O 153 55 CF3 H H H H H H OCF3 H H OC2 H5 O 95-98 56 H CF3 H H H H H OCF3 H H OCH3 O 160 57 CH3 H H H H H H OCF3 H H OC2 H5 O 113 58 H H H H H H H OCF2  CHF2 H H OCH2 CH O 101-103 59 H H H H H H H OCF2 CHF2 H H OCH2 CF3 O 137-139 60 F H H H H H H OCF2 CHF2 H H OC2 H5 O 116 61 F H H H H H H OCF2  CHCl2 H H OC2 H5 O 114-116  62 F H H H H H H ##STR13##  H H OC2 H5 O 106-108   63 F H H H F H H SCF3 H H OC2 H5 O 96-98 64 F H H H H H H SCF2 CHClF H H OC2 H5 O 89 65 F H H H F H H SO2 CF3 H H OC2 H5 O 112 66 F H H H H H H NO2 H H OC2 H5 O 155 67 Cl H H H H H H NO2 H H OC2 H5 O 161 68 F H H H F H H NO2 H H OC2 H5 O 165 69 F H H H Cl H H NO2 H H OC2 H5 O 160-162 70 Cl H H H Cl H H NO2 H H OC2 H5 O 170 71 F H H H H H H CF3 H H OC2 H5 O 131 72 F H H H Cl H H CF3 H H OC2 H5 O 115 73 Cl H H H Cl H H CF3 H H OC2 H5 O 122-125 74 F H H H H H  C(CF3)2 OH H H OC2 H5 O oil 75 F H H H F H H C(CF3)2 OH H H OC2 H5 O oil 76 F H H H H H H COOCH3 H H OC2 H5 O 165 77 F H H H H H H C2 H5 H H OC2 H5 O 116 78 F H H H H H H C(CH3)3 H H OC2 H5 O 165 79 F H H H H H H Cl H H OC2 H5 S 134 80 F H H H H H H OCF3 H H SCH3 O 134 81 Cl H H H H H H OCF3 H H SCH3 O 131-132 82 Cl H H H H H H CF3 H H SCH3 O 159-160 83 F H H H H Cl Cl H H H OC2 H5 O 105 84 F H H H H Cl CH3 H H H OC2 H5 O 110 85 F H H H H F H F H H OC2 H5 O 73 86 F H F H H F H F H H OC2 H5 O 71 87 F H Cl H H F H F H H OC2 H5 O 105-106 88 F H H Cl H F H F H H OC2 H5 O 103 89 F H H H Cl F H F H H OC2 H5 O 95 90 Cl H F H H F H F H H OC2 H5 O 97-99 91 Cl H H F H F H F H H OC2 H5 O 101 92 F H H H H Cl H Cl H H OC2 H5 O 136-138 93 F H H H H CF3 H Cl H H OC2 H5 O 120 94 F H H H H Cl H CH(CH3)2 H H OC2 H5 O 69 95 F H H H F OCF2 CHClF H OCF2 CHClF H H OC2 H5 O oil 96 F H H H H Cl H H CF3 H OC2 H5 O 121 97 CH3 O H H H CH3 O F H H F H OC2 H5 O 104 98 CH3 O H H H CH3 O F H H H F OC2 H5 O 140 99 CH3 O H H H CH3 O Cl H H H Cl OC2 H5 O 200 100 CH3 O H H H CH3 O CH3 H H H CH3 OC2 H5 O oil 101 CH3 O H H H CH3 O CH3 H H H C2 H5 OC2 H5 O oil 102 Cl H H H H H Cl F H H OC2 H5 O 95 103 F H H H H H Cl F H H OC2 H5 O 88 104 F H H H H H NO2 F H H OC2 H5 O 145-147  105 F H H H F H F  ##STR14##  H H OC2 H5 O oil  106 F H H H H H CF3 Cl H H OC2 H5 O 130 107 Cl H H H H H Cl OCF2 CHClF H H OC2 H5 O oil 108 F H H H H H Cl OCF2 CHClF H H OC2 H5 O oil 109 F H H H F H Cl OCF2 CHClF H H OC2 H5 O 78 110 F H H H Cl H Cl OCF2 CHClF H H OC2 H5 O 90 111 Cl H H H Cl H Cl OCF2 CHClF H H OC2 H5 O 70 112 F H H H H H OCF2 CHClF Cl H H OC2 H5 O 128-129 113 Cl H H H H H OCF2 CHClF Cl H H OC2 H5 O 110-111 114 F H H H F H OCF2 CHClF Cl H H OC2 H5 O 117 115 F H H H Cl H OCF2 CHClF Cl H H OC2 H5 O 123 116 F H H H H H OCF2 CHF2 Cl H H OC2 H5 O 130-132 117 F H H H H H Cl COOC(CH3)3 H H OC2 H5 O oil 118 F H H H H H Cl CH3 H H OC.sub. 2 H5 O 105 119 F H H H H H Cl Cl H H OC2 H5 O 96 120 H F H H H H Cl Cl H H OC2 H5 O 105 121 I H H H H H Cl Cl H H OC2 H5 O 109 122 Cl H H NO2 H H Cl Cl H H OC2 H5 O 140 123 Cl H Cl H H H Cl Cl H H OC2 H5 O 120 124 Cl H H Cl H H Cl Cl H H OC2 H5 O 124 125 F F F F F H Cl Cl H H OC2 H5 O 105 126 H CF3 O H H H H Cl Cl H H OC2 H5 O 85 127 H H CF3 O H H H Cl Cl H H OC2 H5 O 85 128 CH3 O H H H H H Cl Cl H H OC2 H5 O 143 129 H NO2 H CF3 H H Cl Cl H H OC2 H5 O 139-141 130 CF3 H H H H H Cl Cl H H OC2 H5 O 135 131 H CF3 H H H H Cl Cl H H OCH3 O 118 132 F H H H F H OCHF2 OCHF2 H H OC2 H5 O oil  133 F H H H F H CH3  ##STR15##  H H OC2 H5 O oil  134 F H H H H H CH3 CH3 H H OC2 H5 O 89 135 Cl H H H H H CF3 Cl H H SCH3 O 96-99 136 F H H H H H Cl Cl H H SCH3 O 125 137 Cl H H H H H Cl Cl H H SCH3 O 125 138 F H H H H H Cl H Cl H OC2 H5 O 98 139 F H H H H H CF3 H CF3 H OC2 H5 O 140 140 F H H H H H CH3 H CH3 H OC2 H5 O 77-80 141 F H H H H H C2 H5 SO2 H CF3 H OC2 H5 O 102 142 F H H H H F H F Cl H OC2 H5 O 85 143 Cl H H H H F H F Cl H OC2 H5 O 55 144 F H H H F F H F Cl H OC2 H5 O 120 145 F H H H Cl F H F Cl H OC2 H5 O 60 146 Cl H H H Cl F H F Cl H OC2 H5 O 92 147 F H H H H Cl H CH3 Br H OC2 H5 O 210 148 F H H H H Cl H Cl Cl H OC2 H5 O 140 149 F H H H F H Cl OCF2 CHClF CH3 H OC2 H5 O 128 150 F H H H H H CF3 Cl CF3 H OC2 H5 O 164 151 F H H H F H Cl OCHF2 Cl H OC2 H5 O oil 152 F H H H H H Cl OCF2 CHClF Cl H OC2 H5 O 128 153 Cl H H H H H Cl OCF2 CHClF Cl H OC2 H5 O 103-105 154 F H H H F H Cl OCF2 CHClF Cl H OC2 H5 O 103-105 155 F H H H Cl H Cl OCF2 CHClF Cl H OC2 H5 O 123-124 156 Cl H H H Cl H Cl OCF2 CHClF Cl H OC2 H5 O 110-112 157 F H H H H H Cl OCF2 CHBrF Cl H OC2 H5 O 121-124 158 Cl H H H H H Cl OCF2 CHBrF Cl H OC2 H5 O 96 159 F H H H F H Cl OCF2 CHBrF Cl H OC2 H5 O 100-103 160 F H H H Cl H Cl OCF2 CHBrF Cl H OC2 H5 O 118-120 161 Cl H H H Cl H Cl OCF2 CHBrF Cl H OC2 H.sub. 5 O 101-203 162 F H H H H H Cl OCF2 CHF2 Cl H OCH3 O 110-113 163 F H H H H H Cl OCF2  CHF2 Cl H OC2 H5 O 123-124 164 F H H NO2 H H Cl OCF2 CHF2 Cl H OC2 H5 O 113 165 Cl H H H H H Cl OCF2 CHF2 Cl H OC2 H5 O 124-125 166 H H Cl H H H Cl OCF2 CHF2 Cl H OC2 H5 O 155 167 F H H H F H Cl OCF2 CHF2 Cl H OC2 H5 O 120-121 168 F H Cl H H H Cl OCF2 CHF2 Cl H OC2 H5 O 142 169 F H H Cl H H Cl OCF2 CHF2 Cl H OC2 H5 O 149 170 F H H H Cl H Cl OCF2 CHF2 Cl H OC2 H5 O 115-116 171 Cl H F H H H Cl OCF2 CHF2 Cl H OC2 H5 O 132 172 Cl H H H CH3 O H Cl OCF2 CHF2 Cl H OC2 H5 O 138 173 Cl H Cl H H H Cl OCF2 CHF2 Cl H OC2 H5 O 135 174 Cl H H H Cl H Cl OCF2 CHF2 Cl H OC2 H5 O 111-112 175 CH3 O H H H CH3 O H Cl OCF2 CHF2 Cl H OC2 H5 O 104 176 CH3 SO2 O H H H H H Cl OCF2 CHF2 Cl H OC2 H5 O oil 177 CHF2 S H H H H H Cl OCF2 CHF2 Cl H OC2 H5 O 91 178 CH3 H H H H H Cl OCF2 CHF2 Cl H OC2 H5 O 138 179 F H H H H H Cl OCF2 CHF2 Cl H O(CH2)2 CH3 O 118 180 F H H H H H Cl OCF2 CHF2 Cl H O(CH2)3 CH3 O 109 181 F H H H H H Cl OCF2 CHF2 Cl H O(CH2)5 CH3 O 82-83  182 F H H H H H Cl OCF2  CHF2 Cl H ##STR16##  O 131-133  183 F H H H H H Cl OCF2 CHFCF3 Cl H OC2 H5 O 105 184 Cl H H H H H Cl OCF2 CHFCF3 Cl H OC2 H5 O 103-105 185 F H H H F H Cl OCF2 CHFCF3 Cl H OC2 H5 O 94-97 186 F H H H Cl H Cl OCF2 CHFCF3 Cl H OC2 H5 O 103 187 Cl H H H Cl H Cl OCF2 CHFCF3 Cl H OC2 H5 O 90-91 188 F H H H F H Cl OCH2 CF3 Cl H OC2 H5 O 101  189 F H H H F H Cl ##STR17##  Cl H OC2 H5 O 143-145  190 F H H H F H Cl ##STR18##  Cl H OC2 H5 O oil  191 F H H H F H Cl SCHF2 Cl H OC2 H5 O oil  192 F H H H H H Cl ##STR19##  Cl H OC2 H5 O 93-95   193 F H H H F H Cl COO(CH2)6 CH3 Cl H OC2 H5 O oil 194 Cl H H H H H CH3 OCF2 CHF2 CH3 H OC2 H5 O 111-112 195 F H H H H F Cl F Cl H OC2 H5 O 125-126 196 Cl H H H H F Cl F Cl H OC2 H5 O 113-114 197 F H H H Cl F Cl F Cl H OC2 H5 O 98-99 198 Cl H H H Cl F Cl F Cl H OC.sub. 2 H5 O 115-116 199 F H H H H F F F F H OC2 H5 O 127-128 200 F H H H H Cl CHF2 Cl CF3 H OC2 H5 O 148 201 Cl H H H H Cl CHF2 Cl CF3 H OC2 H5 O 103 202 F H H H Cl Cl CHF2 Cl CF3 H OC2 H5 O 81-86 203 Cl H H H Cl Cl CHF2 Cl CF3 H OC2 H5 O 124 204 Cl H H H H Cl Cl Cl Cl H OC2 H5 O 140 205 F H H H H Cl Cl Cl Cl H OC2 H5 O 147 206 F H H H Cl Cl Cl Cl Cl H OC2 H5 O 165 207 Cl H H H Cl Cl Cl Cl Cl H OC2 H5 O 172 208 F H H H F CH3 CH3 OCF2 CHF2 CH3 H OC2 H5 O oil 209 F H H H H F F H F F OC2 H5 O 161 210 Cl H H H H F F H F F OC2 H5 O 150 211 F H H H Cl F F H F F OC2 H5 O 125-128 212 F H H H H F F F F F OC2 H5 O 122 213 Cl H H H H F F F F F OC2 H5 O 110 214 F H H H Cl F F F F F OC2 H5 O 143 215 Cl H H H Cl F F F F F OC2  H5 O 150

The preparation of the compounds listed above is effected in accordance with one of the instructions given below.

Each process variant is illustrated by means of an Example in the Table.

Process variant (a)--Preparation of the compound according to Example No. 14

8.36 g (50 mmol) of ethyl 2-fluorobenzcarboximidate and 6.14 g (50 mmol) of p-chlorophenyl isocyanate were stirred for 4 hours at 20° C. 20 ml of n-hexane were then added and the solid was filtered off with suction, washed with n-hexane and dried.

Yield: 14.3 g (89%); Melting point: 130°-132° C.

Process variant (b)--Preparation of the compound according to Example No. 71

6.45 g (40 mmol) of p-trifluoromethylaniline were added dropwise to 9.19 g (40 mmol) of ethyl N-(chlorocarbonyl)-2-fluorobenzcarboximidate and 4.05 g (40 mmol) of triethylamine in 50 ml of absolute methylene chloride, and the mixture was stirred for 6 hours at room temperature. The organic phase was washed with water, dried with MgSO4 and evaporated on a rotary evaporator, and the residue was recrystallized from n-hexane.

Yield: 12.0 g (85%); Melting point: 131° C.

Proces variant (c)--Preparation of the compound according to Example No. 33

11.95 g (30 mmol) of 6-(2,6-difluorophenyl)-3-(4-trifluoromethoxyphenyl)-1,2,3,4-tetrahydro-2H,4H-1,3,5-oxadiazine-2,4-dione and 100 mg of sodium methylate in 50 ml of absolute ethanol were boiled under reflux for 4 hours, cooled to room temperature and diluted with water, and the solid which had been precipitated was filtered off with suction, dried and crystallized from n-hexane.

Yield: 5 g (43%); Melting point: 90°-93° C.

C. BIOLOGICAL EXAMPLES Example I Spodoptera test

Larvae of the African cotton worm (spodoptera littoralis L III) and petri dishes into which a diet based on agar had been placed were treated in a spray apparatus with a preparation of the active compound at the desired concentration. After the spray coating had dried on, the larvae were placed on the agar diet.

After the desired time (L III up to hatching of butterflies) the mortality of the caterpillars or the hatching of the butterflies was determined as a %. In this case 100% denotes that all the caterpillars have been destroyed or that no butterflies hatched out of the caterpillars.

In this test, using a concentration of active compound of 0.001%, compounds Nos. 16, 18, 20, 22, 23, 24, 29, 31, 33, 37, 40, 42, 71, 93, 102, 106, 107, 108, 109, 119, 123, 152, 153, 154, 155, 156, 157, 158, 159, 162, 163, 165, 167, 170, 183, 184, 185, 186, 195, 196, 197, 201 and 205 exhibited a 100% action.

Example II Musca test

Larvae of house flies, 24 hours old (Musca domestica), were placed in a fly diet which had previously been treated with an active compound preparation of the desired concentration.

After the desired time (L I up to hatching of flies) the mortality of the larvae or the hatching of the flies was determined as a %. In this case 100% denotes that all the larvae had been destroyed or that no flies hatched out of the pupae.

In this test, using a concentration of active compound of 0.01%, compounds Nos. 20, 23, 29, 33, 40, 42, 56, 60, 71, 73, 81, 82, 89, 106, 107, 109, 110, 111, 118, 119, 131, 135, 150, 153, 154, 155, 158, 159, 163, 174, 184, 185, 195, 196, 197 and 215 exhibited a 100% degree of action.

Example III Aedes test

The aqueous preparations of active compound at the desired concentration were put into conical flasks and larvae, 24 hours old, of yellow fever mosquitoes (Aedes aegypti) were then put into the flasks.

After the desired time (up to hatching of mosquitoes) the mortality of the larvae or the hatching of the mosquitoes was determined as a percentage. In this case 100% denotes that all the larvae had been destroyed or that no mosquitoes hatched out.

In this test, using a concentration of active compound of 0.001%, compounds Nos. 3, 4, 9, 10, 14, 18, 20, 21, 23, 28, 29, 31, 33, 37, 40, 41, 42, 50, 51, 55, 56, 58, 60, 61, 62, 71, 72, 80, 81, 82, 93, 103, 106, 111, 114, 116, 119, 126, 127, 131, 135, 137, 138, 139, 142, 143, 144, 146, 153, 154, 155, 158, 159, 162, 163, 165, 167, 169, 170, 173, 179, 180, 182, 184, 185, 187, 195, 196, 197 and 204 exhibited a 100% action.

Example IV Epilachna test

Larvae of the Mexican bean beetle (Epilachna varivestis L III) were treated in a spray apparatus with a preparation of the active compound at the desired concentration. At the same time leaves of bush beans (Phaseolus vulgaris) were immersed in the appropriate solution of active compound. After the spray coating had dried on, the larvae of the beetle were placed on the bean leaves.

After the desired time (L III up to hatching of beetles), the mortality of the larvae or the hatching of the beetles was determined as a %. In this case, 100% denotes that all the larvae had been destroyed or that no beetles hatched out of the pupae.

In this test, using a concentration of active compound of 0.1%, compounds Nos. 4, 9, 20, 23, 29, 33, 37, 42, 51, 55, 71, 72, 81, 83, 84, 94, 103, 119 and 131 exhibited a 100% degree of action.

Example V Oncopeltus test

Larvae of a cotton bug (Oncopeltus fasciatus L III) were put into a plastic beaker together with a dental pellet which had previously been treated with a preparation of active compound at the desired concentration.

After the desired time (L III up to imago), the mortality of the larvae or the hatching of the imagos was determined as a %. In this case 100% denotes that all the larvae had been destroyed or that no imagos hatched out of the last larval stage.

In this test, using a concentration of active compound of 0.1%, compounds Nos. 23, 29, 33, 37 and 72 exhibited a 100% mortality.

Patent Citations
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Non-Patent Citations
Reference
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5139785 *Feb 19, 1991Aug 18, 1992Hoechst AktiengesellschaftPesticides
Classifications
U.S. Classification558/9
International ClassificationC07C317/32, C07C313/04, C07C313/00, A01N47/30, C07C309/76, C07C275/28, C07C275/58, C07C275/50, C07C309/65, C07C335/30, C07C275/60, C07C275/40, C07C325/00, C07C335/26, C07C317/42, C07C275/42, C07C323/44, A01P7/04, C07C275/64, C07D211/14, C07C317/50, C07C301/00, C07C303/30, C07C319/20, C07C317/36, A01N47/34, C07C275/44, C07C67/00, C07C323/31, C07C239/00, C07D295/135, C07C315/04, C07C335/18, C07D295/12
Cooperative ClassificationC07C2101/14, A01N47/34, C07C317/42, C07C275/44, C07C323/44, C07C335/18, C07C275/40, C07D295/135, C07C275/42
European ClassificationC07C317/42, C07C323/44, C07C275/42, A01N47/34, C07C275/40, C07C275/44, C07C335/18, C07D295/135
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